Some thoughts after upgrading to an Apple Watch series 2

I’m a fan of the Apple Watch and I’ve worn my original (series 0) nearly every day since it arrived in May 2015. While watchOS 2 and 3 have been a big help in making the Watch more useful, mine started feeling more sluggish as I used more features and newly native apps more regularly. A little while ago I decided it was time to upgrade, and last week I jumped.

I went from a stainless steel, 42mm, series 0 Watch to a Sport space gray, 42mm, series 2. The stainless steel was just a tad too flashy for me, but somewhere down the road, I’d like to pick up another Watch or two in other colors.

For context, I’ll break out how I use my Watch and what I’ve noticed with the upgrade.

My Watch uses

This is a good place to note that two of my goals for wearing an Apple Watch are to carry my iPhone less and be more present. I get notifications on my iPhone (and iPad) for a variety of things, but I treat my Watch as a sort of “VIP notification safe place,” where only the most important get through. I try to put my iPhone in a bag or coat pocket more often to reduce distractions and be more present around people.

With this in mind, I use my Watch for:

  • Siri – I use Siri quite a bit for many of the typical things, but also some niche stuff: creating reminders and timers, messaging, asking basic information (“how many ounces in a cup” – don’t judge me), starting directions, and controlling our gradually expanding set of Hue lights.
  • Dictation – I dictate a lot of stuff, like new ideas in Drafts, new tasks in Todoist, and replying to messages. Pro tip: some messaging services, like Wire (which offers cross-platform E2E encryption, by the way) allow you to reply to messages from a Watch notification, even if they they don’t have a dedicated Watch app. If you’re concerned about privacy with non-Apple friends, Wire and Signal are much better options than SMS.
  • Notifications – I am continually evolving my strategy here, especially as Watch apps and notifications become more useful. But as stated above, in this context, I think of my Watch as an always-present notification widget for a handful of must-see alerts. It’s with me more than my iPhone is (or ever was), so it works great for my needs here.
  • Location tracking – I check into places with Day One and Swarm, generally. But I also do a fair amount of maps directions, and since I’m a transit or foot commuter, I mostly use my Watch and its wrist-tapping directions.
  • Workout tracking – I’m not a huge runner, but I generally do cardio and weightlifting with Gymatic at the gym 1-3 times a week. On the weekends I also love to take my rollerblades down to Chicago’s lakefront and explore the loop area. I usually do anywhere from 4-8 miles in a session and track the route with RunKeeper.

What’s different with series 2?

Apple did a pretty good job of advertising what’s new in series 2. But if your uses overlap with any of mine, it’s hard to overstate just how significant of an impact those changes can have.


Seriously. Seriously. I recently wrote a piece for Mac Observer about how the new app Dock in watchOS 3 is a huge improvement for Watch app users. But the dual core CPU in series 2 takes it to another level.

Most apps start up very quickly, even if the aren’t in the Dock, and everything feels much snappier. You know that feeling when an old Mac or iPad tips over from being sluggish to annoyingly sluggish, and its replacement feels like a refreshing new world? That, but on your wrist.


Battery life so far has been fantastic. Most days when I put my series 0 on my bedside charging stand, I can have anywhere from 20-40 percent left. Over the last few days, my series 2 has been consistently in the 60 percent range, sometimes more.

Sleep tracking

There is a handful of generally well-regarded sleep tracking apps for Apple Watch. But thanks to the battery life improvements, series 2 is the first time I feel like I consistently have enough juice at the end of the day to properly try one. Upon Federico’s glowing recommendation, I picked up AutoSleep this weekend. We’ll see how it goes.

Water resistance

I know series 0 is supposed to be ok in the rain and shower, and even Tim Cook is on record as saying he wears his in the shower. But the fact that it isn’t officially water resistant always gave me pause.

It could just be my paranoia, but my series 0 seemed to act a little funny after some showers, and I enjoy swimming more often these days. Of course, I don’t need to wear my Watch in the shower or pool, but I’ve found it surprisingly useful. Like a lot of folks, I feel like I have some of my best ideas in the shower, so being able to fire off a transcription into Drafts for parsing later has been really useful.

It feels good to have official word that I can wear my Watch in every water-related setting I care about—not to mention warranty and AppleCare coverage. Performance has been great, and that occasional post-water behavior wonkiness is gone.

I’m glad I spent the money

In case it isn’t obvious, I’m happy I spent the money on a series 2 (though, for the record, I’m going to eBay my series 0 to recover some of the funds). I use mine a lot and the new features have made it well worth it to me. I’m not too worried about a series 3 arriving this year; if I had to guess, that feels like a 2018 thing to me.

But even if a series 3 shows up this year, I’m still planning to eventually pick up one or two more Apple Watches somewhere down the road (probably an aluminum and/or gold, possibly even a rose gold). I like watches as a fashion statement, and I was already in the middle of picking up a second old school watch when Apple released one.

If you’re curious about the series 2, I hope this piece helped. But you can always ask me questions on Tumblr and Twitter, and I’ll answer as best I can.

Here's a sample of the Finer Things in Tech Newsletter

If you haven’t seen it yet, I started a weekly Finer Things in Tech Newsletter. For a while, I’ve wondered whether email would be a great format for the kind of bite-sized tips I like to publish here, and so far it’s doing pretty well. 

However, since it’s a newsletter, I’m not publishing it online yet. I’m not sure I will, I’m still new to all of this. But I can give you a sample of issue 2 that went out this week.

If you like the cut of this newsletter’s jib, you can subscribe here. I aim to get it in your inbox on Mondays by 5:30am US central time. I’m also working on a few occasional goodies for future issues, but there will be more to say about that later.

As always, thanks for reading.

iMessage apps have become pretty interesting and useful

Not stickers, apps. I’ve been a sticker proponent for quite a while, as stickers have been a massive (and profitable) hit in other countries for years. They also just make people happy, and in a world like this one, we need more of that. But some apps like Line attribute most (if not all) of their attraction and impressive revenue to stickers. Apple and iMessage basically just closed a five-year gap there.

iMessage apps are different. They appropriate functionality, which lives elsewhere outside of iMessage, and place it right in the conversation with you. For a while, I figured “why not just open that app and tap a share or copy link?” But tinkering with two iMessage apps helped things click for me: Pocket and Fandango.

They remove friction from switching apps to grab content, a link, or even functionality, and keep that stuff right there with me and my friends. There’s something useful about not having to break away from a conversation to go get this stuff.

In the case of Pocket, I save a lot of links there to either read or share with the Pocket community. Now, when I’m chatting with friends in iMessage, those links are just a couple taps away with the Pocket iMessage app, complete with rich media previews.

Fandango for iMessage gets even more interesting. You can go through the entire process right there in an iMessage—pick a movie, a day, choose from your favorite theaters you’ve marked in the app, buy tickets with Apple Pay, pick seats (at theaters that do reserved seating), and send a rich media preview to your friends, all right within the app (I think it can share the Apple Wallet ticket pass to the chat, too. But I’m not buying tickets just to verify for this post 😄).

Besides covering the big tasks of finding a showtime and buying tickets, Fandango’s iMessage app makes many of the little details of organizing an outing like this much more convenient—telling people which theater, offering directions, and sharing a link to find out more info.

Now that these two apps clicked for me, I flipped the switch on a bunch more iMessage apps to see if they’re a good fit as well. Copied and GIFwrapped are good candidates for sticking around, so is Citymapper and its list of recent, shareable locations you’ve saved or searched. There are a few others that I deliberately added to my first or second page of iMessage apps for testing. It’s a big help for me in making them convenient enough to use on any kind of regular basis. We’ll see if they stick, too.

If you haven’t bothered much with iMessage apps, now might be a good time to give them a look. Like Watch apps (especially after watchOS 3), I think developers (and us!) just needed some time to understand the platform and put it to good use.

Some of the apps are getting pretty polished, fast, and useful. I may have my gripes about iMessage, but at least it finally started to compete with the industry in becoming much more useful beyond sharing text and photos. I think iMessage apps have become one of the many little ways that iOS is moving beyond the Mac in not just interestingness, but genuine utility for regular folks.

The new Finer Things in Tech Newsletter debuts Monday, March 20

I realized I can't keep floating ideas or pouring over details or second-guessing myself over the newsletter, I need to just get it out there and see what happens!

So fine, we're doing this.

On Monday, March 20, I will publish the first issue of the all-new, never-before-seen, 100% shiny and chrome Finer Things in Tech Newsletter. Each weekly issue will be a handful of bite-sized, quick-to-read, yet supremely useful tips on how to get more out of your tech and apps, how to work smarter, occasional links to some great non-news tech musing around the web, and some surprise goodies I'm working on rounding up for you.

I've had this idea for a couple years now, as I started wondering if a newsletter would be the perfect format for the type and style of tips that launched Finer Things in Tech in the first place. Let's find out, shall we?

Subscribe to the newsletter here and share this link with all your friends and clients. Maybe your boss, too. Heck, try working it into a Reply All at work, see what happens.

I'm really excited about this, and I can't wait to hear what you think. As always, thanks for reading.

The Finer Things in AirPods

Apple’s new AirPods have quickly become my favorite headphones I’ve ever owned. They have their shortcomings, but their excellent array of features greatly outweigh the cons for me.

I received mine just before Christmas, and there’s barely a day I leave the house now when they aren’t with me. In that time I’ve found AirPods to have some unexpected advantages and perks, so I’d like to dig into some of the details of what makes AirPods a great set of headphones.

They stay in through many kinds of physical activity

I’ve run and lifted with them at the gym. I also live and commute with them in Chicago, which means I’ve occasionally whipped my head around to check traffic or avoid someone rushing down the street. To my surprise, they stay in great.

You can opt to use just one AirPod like a ‘traditional’ Bluetooth headset

It’s really useful for phone conversations, podcasts, or listening to Anchor stations. It’s also discreet for when you’re at a social or other function and just want to quickly and quietly listen to or watch something.

If your pants have a ‘watch pocket,’ AirPods probably fit in it

I wear guy’s pants, and they all have had that tiny little pocket just above the right pocket (apparently, it was originally for pocket watches and dates back to at least 1879). These days I wear my Watch and, as it turns out, the AirPods case fits just fine in my watch pocket. Hence, they almost always leave the house with me now, just in case, as I usually keep them by my wallet and keys.

You probably don’t need to make space for them

I think it’s worth noting separately that AirPods don’t take up much space. You don’t need a separate bag to bring them with you in most cases, and they barely need any room in most bags and tech ensembles. I have a pair of Jabra Revo Wireless and similarly designed Beats Solo3s (which I’m eBaying soon). They certainly have their perks, but even folded up, they practically took up half my backpack.

Space is important. The fact that AirPods barely take up any is refreshing.

Total battery life is insane

A lot of the initial coverage focused on the ‘5 hours on a charge’ bit for the AirPods themselves. But in practice, I don’t use mine for nearly that long in a sitting. I use them for a phone call, then some music while I work, then put them back in the case to charge. I take them back out to take a break and play a round of Vainglory, or maybe a podcast or two while I commute somewhere. Put them back in the case.

There’s a cadence to my usage, which means my personal, total perceived battery life easily hits that 24 hour mark (so far I’ve only goften them in the red at 11 percent once). I’ve owned a few wireless earbud-style headphones over the years, but none of them can touch that. Not even Apple’s other brand new wireless earbud-style headphones, the BeatsX at 12 hours.

If you’re iOS only, you can reach the Charger Singularity

When I leave the house to work in a field office or co-op, I usually bring my iPhone, AirPods, and iPad (I use my Mac much less these days). This allowed me to achieved Charger Singularity—all I carry is a Lightning charger now (the 29-watt block charger with Apple’s longer cable for fast charging). It’s pretty nice.

Not for everyone, but they’re great for me

The AirPods certainly aren’t perfect for everyone; what is? But they fit my needs very, very well, and I’m an extremely happy owner. I hope these tips and perks help if you have a pair or decide to pick one up.

Subscribe to the Finer Things in Tech newsletter, coming soon!

I’ve been toying with the idea of publishing a newsletter for a while, and now it’s happening.

Subscribe to the all-new, upcoming Finer Things in Tech Newsletter!

The Finer Things in Tech Newsletter will be a weekly handful of bite-sized tips to help you get more out of your tech and apps. Some issues might center on a theme, others might include a couple links to good, non-news reading around the web. I’m also trying to score a few goodies to include from time to time.

Each issue will have space for a sponsor, but in the form of a tip, just like everything else in the issue. I want every line of this newsletter to be informative.

My main goal is to bring you a tremendously useful, yet short and easily digestible newsletter of useful tips and apps. If that sounds up your alley, I’d love for you to subscribe to the all-new, upcoming Finer Things in Tech Newsletter! Also, if you know anyone who might enjoy this newsletter, I would really appreciate it if you passed the word along.

As always, thanks for reading!

Apple Watch faces for work, play, music, and every occasion in between

I wear my Apple Watch seven days a week, but recently realized that I do so for different reasons throughout the week. These days, it’s with me at least as much as, if not more than, my iPhone, so I decided to explore how I can make my Apple Watch even more contextually useful for each day’s tasks. After experimenting with the new watchOS 3 faces features, and getting a pair of AirPods, I’m getting the urge to break into song.



A whole new world

In watchOS 3, Apple added the ability to quickly swipe between multiple Watch faces. After playing with this effortless switching, I realized that it feels like swiping between pages of apps on an iPad or iPhone.

Now, I’m also the type of person who organizes my app pages by task or context. Page 1 is my most important personal + work apps, page 2 is for my photo, video, and music hobbies, page 3 is strictly work apps, and so on. Once I combined these two ideas, things started to click.

I got my Apple Watch in its early days, and my go-to face has always been an info-dense (for a watch, anyway) dashboard of my day’s events, tasks, and physical activity. I was looking for a way to be more present and cut down on how often I have my phone in my pocket or hands. This face was a great solution.

Around the beginning of December 2016, I decided to add a “relax mode” Watch face. It uses one of the new animated jelly fish backgrounds with only a clock and Drafts complication for quickly dictating ideas to revisit later. In the evening or on weekends when I had little-to-no work to finish, this “no work stuff allowed” face would serve as a nice on-demand reminder that it’s chill time.

After my standard work-based dashboard face, this was my second purpose-built Watch face. It worked great and made me think about Watch faces as the new app pages – quick access to a few apps for related tasks. Now that faces are so easy to switch between, what other occasions, tasks, or purposes could use a Watch face?

The Setup – Watch faces as the new app pages

It was easy to go down the rabbit hole, separating my days or even portions of them into all kinds of categories and “modes,” for lack of a better word. But I eventually settled on a few general purposes for which I think an individual, customized Watch face might be useful. Here we go, in order of appearance in the gallery below from top left to bottom right.

Music – The perfect AirPods companion for me

I love my AirPods, they go everywhere with me now. Pro-tip for pants people: the case probably fits in that little change pocket just above your right pocket.

However, I’d say around 50-60 percent of the time, I’m listening to a playlist I created or something I’m exploring from Apple Music, which means spurts of skipping. Since I’m trying to keep my phone in a pocket or, ideally, my bag or on the shelf at home more often, I realized I could create pretty quick access to media controls with a Watch face.

I didn’t expect to turn this music dashboard into what is technically now the first Watch face in my lineup, but there it is. Now I can quickly swipe a couple times to control my AirPods music without digging out my phone or fumbling with other app controls.

There’s a catch here, though, and I might have to tinker more. The music complication in the middle of this Modular face doesn’t have controls, it’s really just a nice big tap target for me to open the Music for Watch app and then start controlling stuff (tip: to quickly get back to your Watch face from an app like this, double-press the crown). I’ve considered adding a smaller complication to other faces, and maybe I simply don’t need this one. We’ll see.

Ultimately, I wish I could have one of two things. The first, and my preference, is an update to the Watch Control Center to give it multiple pages like iOS 10 added for iPad and iPhone. Also like iOS 10, it could remember the last page I picked, so swiping up on my Watch during a good music session could always display media controls.

Failing that, I could also go for a mini-music dashboard Watch face, or at least the complications we could use to build one. It could display the current thing playing and controls right on the face; no switching away from the clock to other apps. With the popularity of AirPods and how well they go with a Watch (iPhone not necessarily required), I wouldn’t be surprised if this arrives soon. Yes, I’ve submitted this idea to Apple’s feedback and bugreporter sites.

General purpose – Modular face

My standard face that I’ve had practically since day one with watchOS 1. Like my first iPhone and iPad app page, this is quick access to some basics for most days: date, Timepage in the middle (my new favorite calendar app), Drafts, Activity, and Weather Underground.

Work – Modular

This feels self-explanatory. Todoist in the upper left, Timepage again in the middle, then Drafts, Hours for time tracking, and AnyList in case there are errands I can run during my day. I’d prefer to have Trello in the lower right, but they don’t have a Watch complication yet. Hopefully soon.

Personal – Modular

A face for non-work personal days of errands, friends, and chores around the house. Timepage in the upper right, Todoist in the middle, then Drafts, AnyList, and Activity. I feel like I want to tinker with this one more, maybe replace Activity with something else. But for now it’s pretty good.

Activity – Analog

I deleted most of the default faces, but kept this one. On the (gradually more frequent) days where I exercise, I like having quick access to a dashboard of the health apps I use. Right now I use a mix of Apple’s workout tracking and RunKeeper, though I’m getting really unhappy with the latter. Details aside, I love having this big colorful view of how much exercise ass I’m kicking.

Relax – Motion

This is the chill out face I mentioned earlier, and in some ways my favorite. It isn’t just the pretty video—I love having an always-available dashboard, of sorts, which reinforces the idea that right now is my time, and I can do whatever I want.

Relax 2 – Photo Album

I sync my favorite photos from Apple Photos to my watch. This face is just an alternative for relaxing, and the only one that doesn’t have Drafts. I sacrificed it in the name of having a more complete view of my photos.

A work in progress

This is new territory for me, so I’ll continue to tweak my Watch faces and replace apps or switch faces altogether. Overall though, I’m really happy, as I feel like I’ve unlocked a new level of Watch usefulness. I hope some of these ideas can do the same for you.

3D Touch is the new Option key

Back in my early Mac days, when I was hungrily learning my way around the OS, I remember the little joys of exploring all the tricks and time-savers that holding the Option key would unlock. These hidden perks usually weren’t documented anywhere; you had to just click around while holding the Option key or find a blog post round up like the ones I used to write.

3D Touch on an iPhone 6S or later is the new Option key.

Like the perks of the Option key on macOS, the handy and time-saving gestures of 3D Touch are hidden, yet pretty easy to discover if you just take a second. I find them all over the place, from Airmail‘s icon, to notes in Evernote, to individual days in Timepage.

My favorite is using it on Apple’s stock keyboard—it allows you to drag the cursor around and place it right where you want. On iPad, place two finders on the keyboard to get the same effect. This also works on the emoji keyboard.

Just like switching to use Option more often in my Mac workflow, it simply took a little time for me to get natural with 3D Touch. Now, I’m not saying it’s for every situation or feature. In Airmail, I can swipe left to trash and right to archive—using a 3D Touch, swiping up a little, then tapping archive or trash from the options that appear below, doesn’t stack up very well.

But a 3D Touch on a day in Timepage has a ‘Clear My Schedule’ option for that day. When selecting multiple items in Photos, or picking a photo in many in-app photo pickers, I can 3D Touch one to preview it instead of killing the current action. I’ve even come to prefer 3D Touching links in Safari and Tweetbot, as it feels faster than waiting for the in-app browser to slide in and load the page. Plus, getting out of the page is a simple lift of the thumb, which also feels faster than moving to tap Done.

It was fun exploring where Apple and developers hid all sorts of Option key perks. Feels like that little torch has been passed on to iOS with 3D Touch. I like it.

From Dropbox to iCloud Drive: a review and some thoughts

My Dropbox-to-iCloud Drive experiment has gone pretty well overall. Both were charging me $10 per month for 1TB of space, but now that I moved everything to iCloud Drive and pulled Dropbox back down to the free tier, I get to save $120/year.

For personal uses, iCloud Drive has performed pretty well for me the past couple months. The speed of saving files to and retrieving files from iCloud Drive feels on par with Dropbox on both iOS and Mac, thanks in part to improvements in macOS Sierra. However, I should restate that I do much less collaboration with raw files these days. I create and manage nearly all of my work in apps and services like Ulysses, Quip, Todoist, and Trello, then share or publish it with others in online systems like WordPress (this site), Weebly (my personal and business sites), Quip, or Google Drive. Of course, your mileage will vary.

The few raw files I still work with are things like PDF books I download, or media resources I snag from Unsplash, Envato, and elsewhere for content and blogging. If I need to receive files, I can of course still use my free Dropbox space, or I can visit Dropbox share links in a browser on any device. When it’s time to share files with others, Dropbox can still work, but so can Droplr.

Others who have made this transition told me there’s a noticeable performance boost to be had by uninstalling Dropbox from a Mac, which I just did yesterday. They weren’t kidding.

I’m pretty happy so far. I still use my Mac for a dwindling handful of tasks at least a couple times a week, so it downloads everything from iCloud (and still Dropbox) and backs up to my Time Capsule, just in case. But at this point, I’m feeling pretty good about simplifying my cloud services and saving money.

All that said, iCloud Drive is not without its drawbacks. Here are a few problems and speed bumps I’ve hit so far, and yes: I’ve filed radars (sometimes multiple) for all of these.


The ‘Save to iCloud Drive’ app extension is great, but

The “Save to iCloud Drive” dialog uses a terrible file viewer that is hard wired to 1) a list view, with no icon view option, and 2) have all folders and sub folders opened. It makes scrolling even a modest file library nearly unusable. I am quite disappointed that this shipped at all, especially since the iOS 9 app extension file viewer was much nicer. To work around this problem, I created an @Inbox folder on my Mac, which floats it to the top.

Oh yeah, folders

Update: Turns out I was wrong, you can create new folders in iCloud Drive for iOS. It’s arguably a little hard to find, but easy to use once you do. Tap the select button in the upper right, then a New Folder button appears with the other file management controls.

There’s no way to create a new folder on any iOS device. You need a Mac, because it is apparently still 2010.

Also, tags

Finder on the Mac has supported tagging files for a few years. While you can sort folder contents on iOS by these tags, there is no way to apply tags on iOS. You need a Mac, because it is apparently still 2010.

App folder clutter

All apps that store files in iCloud Drive are hard wired to have their own folders in the top-level directory. This means I have to scroll past folders for Byword, Cinemagraph Pro, Mindnode, etc. just to find my Documents or Resources folders. It would be great to have the option to collect those files in a specific folder, such as /Apps.

Restoring deleted files

This is a ding on both Dropbox and iCloud. iCloud Drive has what I think is a fairly standard a 30-day retention policy, kinda like Photos does for your media. But to restore files, you’re stuck like Dropbox: you need to jump on a Mac or PC to use the web interface. Also like Photos, this is functionality I believe should be built right into the app, especially since won’t let you get into any of the apps if you visit on an iOS device. While you can use the ‘Request Desktop Site’ option, I doubt it works well on iOS.


A while ago I got tired of suffering death by 1,000 clouds. I’ve canceled a couple of small services since then, but this is one of the largest changes and savings I can make. For my needs, it’s gone well so far, though I certainly hope Apple pays more attention to iCloud Drive to make it a more viable competitor in this space. Things like file sharing and competent file browsing tools are a must, and I’m hopeful Apple can close those gaps soon.

Progress update: My Dropbox to iCloud Drive experiment

To catch everyone up: A while ago, I wrote about paying for too many clouds that are getting too Venn-diagram-y for my comfort and wallet. Dropbox and iCloud are two of my most expensive and overlapping clouds, but I can leave Dropbox easier than iCloud, so I decided to try just that.

My plan is:

  • Phase 1: copy the roughly 70GB of stuff I have in Dropbox to iCloud Drive
  • Phase 1 part deux: backup the hell out of everything
  • Phase 2: test the hell out of changing my file-based workflows with iCloud Drive
  • Phase 3: Delete everything from Dropbox, except folders I’m collaborating on
  • Phase 4: fall back to Dropbox’s free tier for what little collaboration I still do with it, and to support the apps I use that sync only via Dropbox

Because of how much stuff I have, I’ve been paying $10 per month per service, so I hope to save $120/year.

If 70GB doesn’t sound like much to you, I have about 110GB of photos in iCloud Photo Library, and probably 1+ TB of purchased iTunes music and movies, and around 440 apps from over the years. But I generally don’t consider that stuff “data I need downloaded and backed up,” at least not in Dropbox or iCloud Drive. I have an external iTunes drive that I hook up once every few months, and I download my recent purchases ‘just in case.’ I also have a Time Capsule at home to which I backup my entire Mac, including both Dropbox and iCloud Drive, also just in case.

Part of the impetus for this experiment, beyond saving money and simplifying where I store stuff, is that I realized most of my collaboration now happens in Quip and task apps like Todoist, Trello, and Basecamp. In other words, I mostly collaborate in systems and apps these days, not raw files and folders. Being that I’m a much bigger fan of using various apps for most of my work, this fits my style. Obviously, your mileage may vary.

Status report

As of about September 23 or so, phases 1 and 1 part deux are done. I finished copying all my Dropbox files into iCloud Drive, then ran a Time Machine backup to cover my ass. Then another, mostly because I’m human and I still don’t trust these things. Also, no, I’m not blind or deaf to the, shall we call it, “ever so slightly turbulent road” iCloud has taken to get where it is today.

I am also what I would consider a pretty good way through phase 2—testing iCloud Drive for my day-to-day needs. I’m mostly iOS these days, so when I do things like scan travel receipts into a PDF for expenses, I now save to a folder in iCloud Drive. On my Mac, I moved the Dropbox item in the Finder sidebar down, and put iCloud Drive in its place.

So far, it’s gone pretty well. Saving and accessing files in iCloud Drive feels about as fast as Dropbox. Watching the file upload/sync process to iCloud Drive feels fine too.

Of course, one major feature iCloud Drive lacks for my needs is collaboration—it can’t share folders or even individual files with others (sure, MailDrop is a smart feature that might suffice in some cases, but.. eh, it’s just not the same). Being that my content strategy business is client-based, it’s a prime argument for why I still should keep around at least a free Dropbox account for the near future. I also have a handful of apps that still sync only via Dropbox, so I hope the free tier accommodates them too. Gradually, I’ll ask those devs to support iCloud Drive (if they don’t already), and possibly seek out alternatives that do. But if the free Dropbox space works for now, it isn’t a high priority, at least not just yet.

Naturally, I hope Apple is working on addressing these collaboration features which pretty much feel like a necessity these days. Considering it already has features like calendar sharing and a whole feature umbrella called Family Sharing, I think Apple gets it. I just want to see it move faster; it’s already way behind here.

I feel pretty good about moving ahead with phase 3 and 4, so I might take care of that this weekend. I’ll write a follow-up once the dust settles.